


Ash Wins

by PaperFox19



Category: Pocket Monsters | Pokemon (Anime)
Genre: Anal Sex, Humiliation, M/M, Mind Break, Multiple Orgasms, Oral Sex, Sex Toys, Watersports, Yaoi
Language: English
Status: Completed
Published: 2020-04-12
Updated: 2020-04-12
Packaged: 2021-03-01 17:20:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,710
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23610685
Author URL: https://archiveofourown.org/users/PaperFox19/pseuds/PaperFox19
Summary: It had been a bet, and after a 6 on 6 battle Ash had won. Now Gary had to do what Ash said, and boy is he gonna learn a little about himself.
Relationships: Ookido Shigeru | Gary Oak/Satoshi | Ash Ketchum
Kudos: 52





	Ash Wins

**Author's Note:**

> Old Fic Repost

Warning this fic contains elements of water sports if you don’t like this you may not like this fic

Ash Wins

It had been a bet, and after a 6 on 6 battle Ash had won. Now Gary had to do what Ash said, and boy is he gonna learn a little about himself.

-x-

Ash stood with his Pikachu, he had just beaten Gary Oak, his long time rival in a 6 on 6 battle and not only did he win he had 3 pokemon to spare. The two had made a wager that the winner of thi battle had to do whatever the other said, for 24 hours. “Looks like you lose, Gary.”

“Well I admit you sure have gotten better. What do you say best two out of three?”

“No chance you lost now pay the bet.”

“Fine I promise to do what you say.”

“Good, now strip.” Gary blushed but obeyed.

Ash watched in satisfaction as Gary started removing his clothes. “Hold on,” he said before Gary could take off his underpants. “I want you to do a strip-tease for me.” Gary cursed. The shirt came off slowly, revealing his sculpted chest, doing this in front of Ash had stirred foreign feelings inside him. His nips had gotten all perky.

He tossed away the shirt, and he stretched his arms up, flexing his body and exposing his smooth pits. He wiggled his hips as he kicked off his shoes. Feeling Ash’s eyes on him Gary got more and more excited though he didn’t know why. ‘This is humiliating.’ he lowered his pants and exposed his tighty whities. He bent over to remove his socks, and Ash grinned as Gary’s booty wiggled from side to side as each sock got removed.

Finally the last garment, he hooked his fingers and tugged them down. Much to his humiliation his dick sprang up fully erect. It stood proudly at 5 inches long. “My Gary, does stripping for me turn you on so?” he flicked Gary’s cock, it bounced and the brunette moaned.

“N-n-n-n-nooo!” he clenched his fists and tried to hide his shame.

“Don’t lie to yourself,” Ash said before slapping Gary’s bare ass. “Now try again. And this time, try telling the truth.” the brunette yelped, and his cock lurched.

“I-I-I-I- (gulp)” he was shaking. “I can’t, I confided in the girls I traveled with and they said I was gross for thinking…” he bit his lip. Ash pulled Gary in for a kiss, he licked his lip and the boy gasped allowing the raven haired boy to deepen the kiss. Gary’s eyes rolled up and he moaned into the kiss.

“Relax, for now let’s play I’m sure you will find the answer for yourself soon.” his hands came around and began massaging Gary’s chest, his rough fingers teasing the skin, and each time they brushed his nipples Gary let out a lustful moan of pleasure. Ash leaned up to the boy’s ear, his hot breath tickling him. “Besides Gary, I know things about you that nobody else will ever know. For instance, I know you have a watersports fetish, I know you still have a crush on me from our childhood, and I know you secretly dream of me dominating you. Well, it’s high time I claim my property. Am I right?”

“How did you hear that?”

“A little birdy told me, didn’t you ever wonder what happened to My Pidgeot, I’ve had him keeping an eye on you. My Noctowl would keep an eye on you at night.” he pinched Gary’s nipples. “You moaned my name in such a way while you slept. You would cum so hard you pissed yourself, you used your liquid as lube to play with your ass.” Gary hung his head, but Ash raised him up

“You must think I’m disgusting.”

“I think you’ve been without for so long, and got some bad advice from bitches who cared more about stroking your ego, than stroking this.” Ash gripped his penis and caressed it and Gary moaned. “I find you hot, see!” he brought his hand down to feel the bulge in his pants. Gary shuddered feeling his confined hardness. He felt the itch inside his ass, the itch his fingers couldn’t satisfy.

“I’m yours Ash not just today, but every day if you’ll have me.”

“Oh Gary, you were always mine. I’ve just been waiting for you to come to your senses. And no, I don’t think you’re disgusting. Every time I hear about you using your piss to lube yourself, it only makes me want one thing. And that’s to fill you with mine.” Gary shuddered, every fantasy, every naughty secret he held inside was now spilling out in bliss. His pre overflowed and got smeared all over his erect penis.

Ash’s hand dropped from his nipple and went to play with Gary’s tight hole. It’s been awhile since he teased himself, but Ash’s fingers felt so much better. “Are you imagining me peeing in you right now, Gary?”

“Y-y-y-y-y-y-yessss!” he bucked back onto his fingers.

“I can see your more honest now. Let’s reward that honesty.” Ash released Gary’s cock and used his free hand to undo his pants and lower his boxers, Ash’s mighty cock sprang up and Gary shivered seeing his fat 9 inch long dick.

“You want it, but I want you to beg for it.”

“Please Ash, I want you inside me, to feel you filling me is my dream I beg yo make my dream a reality.” He moaned his back arching with need.

“Don’t be vague,” Ash said. “I want to hear you say exactly what you want me to do with my cock.” Said cock was sliding between his ass cheeks, so Gary felt the fat meat against his hole.

“Fuck me, pound me into the ground, and when you’ve ruined my hole mark me with your piss and cum!”

“From now on, whenever I need to pee, I’m going to use your ass. Is that what you want?”

Gary shivered, he could see the news blasts now. Gary the pride of pallet town happily accepts his role as Ash’s personal urinal, and loving every second of it.

“Well, it looks like you DO want it. Am I right?” Gary nodded. “Alright then!” he pushed his dick inside and Gary cried out in pleasure, his hole stretched wide over Ash’s penis.

“Ahh fuck yes!” Gary came hard, blowing his load all over himself.

“Gary, I didn’t say you could cum yet. Man, you’re just as stubborn as Cilan and his brothers.” Ash collected some of his cum on his fingers and stuck them into the brunette’s mouth. Gary sucked them, moaning hotly. “Well this is your first time I’ll let it slide once but from now on you ask for release understood?” Gary nodded. “Good boy.”

Ash began to move, pulling out to the tip only to thrust back in making Gary groan in pleasure. “I see you at least catch on to the program pretty quick. It took Chili at least two days to get it.” he played with Gary’s nips and the brunette groaned.

“Please Ash feels so good.” his dick was hard again, and began bouncing with every thrust.

“This is a sight I never thought I’d get to see. And I’m loving every second of it.” Gary’s eyes were glazed over and he was drooling from the stimulus he had craved for years. His ass kept squeezing the boy’s thrusting cock increasing the pleasure between them.

“You’re taking to this rather well. I guess you’re ready for some of my cum?”

“I’ve wanted this so long, please give it to me, breed me!”

Ash grabbed Gary’s hips and slammed forward as he hit his orgasm. “Oh yeah. I never get tired of a breeding session.” he playfully slapped his ass as he came. Each spurt rammed his prostate again and again, the pleasure driving Gary mad.

“Please need to cum!”

“Do it Gary, cum and accept your place as my bitch.” Gary came hard, harder than he ever had in his life. “Very good, my pet. And I’ll be sure to get you a collar like the others.” Gary was barely listening still high on pleasure. “Now then what we’ve both been waiting for.” Ash let out a sigh as he emptied his bladder.

Hot piss poured into Gary’s bowls and the boy moaned at the feeling. Piss and cum mixed together and filled Gary to the brim, Gary couldn’t help it he came again the release washing over him like a tidal wave and he was gone.

Ash grinned and pulled out, Pikachu was over in a second bringing a butt plug from his bag. “Thanks Pikachu.” he pushed it in and Gary moaned. “Now let’s get him home to the others.”

-x- Omake -x-

Gary had a collar around his neck, the tag had pet – urinal on it. Gary loved his new life and his brothers in arms. The pets consisted of Surge wearing dog ears and a dog tail dildo stuffed up his ass, a cock ring and matching collar adorned him, Paul wearing similar dog ears and tail that matched his hair, Richie was adorned with cat ears and tail, Morty was also wearing cat ears and tail, the thing about the nekos they were so well trained they didn’t need cock rings. The pets all shared the same training, loving Ash’s cum and loved getting pet.

Brock Brawly Marlon and Tate were Ash’s cum dumps, they lived their lives buck naked, with a butt plug stuffed up their asses. These boys got off on taking Ash’s cum inside them and loved carrying his loads inside them.

Nando was special, he got to stay at Ash’s side playing his music and getting rewarded in various ways.

Cilan, Chili, and Cress were Ash’s pets – servants clad in collars and had nice fat dildos stuffed up their ass, and they wore thongs so the strap could ride up on the toy. Gary fit right in with them all, they each had a strong burning love for Ash that Ash let out and accepted in every way. It was a weird set up but it worked.

End


End file.
